Bennifer 101: A Timeline of Jennifer Lopez and Ben Affleck’s Relationship

The summer of 2024 has been…complicated for Jennifer Lopez and Ben Affleck. As they possibly, allegedly, begin divorce proceedings, she appears to be living her Nancy Meyers-esque best life, boating in Italy and biking in the Hamptons, while he’s been riding his motorcycle around Los Angeles. (You know how it goes when you’re hot, rich, and famous.)

These two have weathered pretty much every up and down that that a celebrity couple can, so it’s possible that this latest rough patch is just another bump in the road (they do happen!). While we wait to find out if the break-up rumors are, in fact, real, however, catch up on the full story behind this larger-than-life duo’s decades-long romance.

Act I: Jen and Ben meet (December 2001)

A little film by the name of Gigli began filming in December of 2001, bringing Lopez and Affleck together for the first time. In a recent interview with Variety, Lopez recalled first meeting Affleck during a read-through of the film. “I don’t remember a whole bunch more about it,” she continued, “but I remember being on the set with him every day and loving it.” It’s not every woman that can nab a famous boyfriend while playing a character described as a “lesbian assassin,” but that’s J.Lo’s power for you!

Act II: Jen and Ben’s first musical collaboration (November 2022)

Affleck may be on the record regretting his appearance in the music video for Lopez’s 2002 hit “Jenny from the Block,” but I, for one, can’t get enough of watching the couple lounge on a yacht from a paparazzo’s point of view.

Act III: Jen and Ben get engaged (November 2002)Lopez flashing her engagement ring at the Los Angeles premiere of Daredevil on February 9, 2003.

Photo: Getty Images

It was the ring seen ’round the world: When Affleck proposed to Lopez—at his childhood home in Boston!—with a six-carat pink diamond ring from Harry Winston, fiancées everywhere suddenly found their own fourth-finger bling curiously lacking. “It’s the most magnificent thing I’ve ever seen. I still look at it and kind of marvel at it,” Lopez said of the ring in 2002, when she announced her engagement in an interview with Diane Sawyer. “He was like, ‘I just wanted you to have something that nobody else would have.’”

Act IV: Jen and Ben break up for the first time (January 2004)

After two years’ worth of dodging paparazzi on their date nights—and postponing their September 2003 wedding in Santa Barbara due to the “excessive media attention” surrounding it—Bennifer officially called it quits, with Lopez’s press rep (who deserves hazard pay, by the way) stating simply: “Jennifer Lopez has ended her engagement to Ben Affleck. At this difficult time, we ask that you respect her privacy.” Mere months later, the two went on to promote their film Jersey Girl together, which is a level of “being civil to your ex” that most can only dream of.

Act V: Jen and Ben start hanging out again (May 2021)

I’ve seen a lot of amazing things over the course of my life, but I remain eternally grateful that I was a pop-culture reporter when the news broke that Lopez and Affleck had been spotted together near Affleck’s home in Montana in 2021. By this point—17 long years after calling off their engagement—both had become parents, gone through divorces, and entered high-profile new relationships: Lopez, with baseball player Alex Rodriguez; Affleck, with actress Ana de Armas.

In 2021, shortly after Rodriguez and de Armas had exited the picture, Lopez and Affleck got in touch again over email. “I never shied away from the fact that for me, I always felt like there was a real love there, a true love there,” Lopez told Vogue in her December 2022 cover story. “People in my life know that [Affleck] was a very, very special person in my life. When we reconnected, those feelings for me were still very real.”

Act VI: Jen and Ben engage in some vintage red-carpet PDA (September 2021 to February 2022)Celebrating Affleck’s movie The Last Duel at the 78th Venice Film Festival.

Photo: Getty Images

At the 2021 Met Gala

Photo: Getty Images

At the New York premiere of The Last Duel

Photo: Getty Images

At a Los Angeles screening of Lopez’s movie Marry Me

Photo: Getty Images

If you’re not making out at a red-carpet premiere (or the Met Gala), are you even a newly reunited mononymous Hollywood couple?

Act VII: Jen and Ben get engaged…again (April 2022)

A few things changed between the first proposal and the second (not least among them Lopez’s engagement rock, which went from pink to green), but as of two years ago last April, Bennifer was officially official, and headed toward the altar (again). Lopez described the whole thing in her newsletter, On the JLo: “Saturday night while at my favorite place on earth (in the bubble bath), my beautiful love got on one knee and proposed,” she wrote. “I was taken totally off guard and just looked in his eyes smiling and crying at the same time trying hard to get my head around the fact that after 20 years this was happening all over again, I was quite literally speechless and he said, ‘is that a yes?’ I said YES of course that”s a YES.”

Act VIII: Jen and Ben get married! (July and August 2022)The date was July 16, the location was Las Vegas, and the ceremony was allegedly extremely small (which kind of suits this couple, given their first betrothal famously flamed out amidst near-constant press scrutiny). Then, a month later, they did it again—this time, on Affleck’s 87-acre compound near Savannah, Georgia, where the bride wore three different custom Ralph Lauren Collection dresses.

Act IX: Jen and Ben get coordinating couples’ tattoos for Valentine’s Day (February 2023)If anyone young and impressionable is reading this: Please do not repeat this behavior with your partner, no matter how much you love them—unless, of course, you have tattoo-removal money saved up. In that case, go forth.

Act X: Jen cancels her summer tour amid divorce rumors (June 2024)Photo: Getty Images

Shortly before Lopez canceled the United States leg of her This Is Me…Live Tour in late May—officially to “be with her children, family, and close friends”—People reported that she and Affleck were no longer living together. Then, in June, they listed their mansion in Beverly Hills. For the moment, things are not looking good for the couple—but one can only hope that this is just another chapter in the multi-volume love story that is the Bennifer saga,